Can you blame San Juan for being a little schizophrenic? It's a Spanish-speaking city filled with American businesses and restaurants and a former outpost of a colonial empire that is now responsible for driving most of the Caribbean economy. While it has quite a history, it is often treated as a footnote by the United States because of Puerto Rico's "commonwealth" status. Yet San Juan is more than ready to come into its own as a vibrant city that forms an enchanting bridge between two worlds. San Juan travel is about long nights, sunset cocktails, sleepy afternoons on white chaise lounges and gambling as early (or late) as you want. In modern San Juan, no request is too difficult for the concierge to handle, and no drink too complicated for the bartender to make. Then there is Old San Juan, the part of town where the clock stopped 500 years ago and doesn't appear to have moved since. This is the city of statue-filled plazas, baroque white churches, open gardens accessed through Moorish...See More arches, windy cliffs atop the blue Atlantic Ocean and twisty cobblestone streets that never go in a straight line. Which you chose to inhabit is up to you—or you can do as the San Juaneros who live here do and grab what you like from both. Spanish and English are interchangeable, and you can spend the morning soaking up pre-Colonial African history in one of the city's excellent museums, and then work on your tan in the afternoon. Your evening choices are even more plentiful—casino, trendy nightclub, professional flamenco show, or some dirty dancing to thumping reggaeton? Sure, why not? A night on a San Juan vacation could even include them all—and maybe, during the frenzied Christmas season, a midnight swim for good luck. It's a crazy, hedonistic place, but if you embrace the city's bifurcated personalities, you'll see the options for fun are endless. See Less